Fragmentation of nitrone triflates to 9-membered rings

John A. Murphy, Mohan Mahesh, Gary McPheators, R. Vijaya Anand, Thomas M. McGuire, Robert Carling, Alan R. Kennedy

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

A new fragmentative rearrangement of nitrone derivatives to form 9-membered rings is reported. The fragmentations are triggered when nitrones are treated with triflic anhydride; a C-C bond antiperiplanar to the cleaving N-O bond is activated either by an oxygen lone pair or by an electron-rich aromatic ring. In the former case, further cyclization of the 9-membered intermediate leads to a rearranged condensed ring system, but when triggered by arenes, 9-membered ring amides are isolated.

Original languageEnglish
Pages (from-to)3233-3236
Number of pages4
JournalOrganic Letters
Volume9
Issue number17
DOIs
Publication statusPublished - 16 Aug 2007

Keywords

  • nitrone triflates
  • cyclization
  • amides

Fingerprint

Dive into the research topics of 'Fragmentation of nitrone triflates to 9-membered rings'. Together they form a unique fingerprint.

Cite this